Andrew in Wonderland

Chapter 11: Naughty Night

Andrew lay in bed, restless, for hours and hours. He had had quite the day, yet he couldn't bring himself to fall asleep, not after the incident. He couldn't stop thinking about Lisa, those big golden eyes meeting his own and the touching of their sweet soft lips. The part of his brain that used to shun such thoughts seemed to have mostly given up and given in. Now he wanted nothing more than to do it all again. His heart pulsed and his clitty throbbed in agony as he recalled their bodies ladened in soft frills grasping each other. With all this pent-up desire inside of him, Andrew could take it no longer. He sat up in bed and glanced around.

The room was completely dark and his eyes took a few seconds to acclimate. All the other sissies lay in their beds, row by row in graceful slumber. Nobody but him was awake. He looked up at the ceiling. Two security cameras hung from it, one on each far corner.

Andrew thought it impossible for them to see him, the room was far too dark, he second-guessed himself for a second, but his horniness continued to flood his thoughts and he disregarded it. He looked down at himself, he wore only his pullup and a light blue nightgown. He lifted the gown with one hand and began to slowly creep the other down into his pullup.

It wiggled its way down past his cleanly shaven crotch and onto the thick plastic cage which covered the thing he had used to call his penis and began to caress it up and down like had used to do all the time before arriving in Wonderland. He felt some minor pleasure initially, but this quickly faded. The cage was far too thick for any meaningful touching, at least with his hand. He barely felt anything at all.

Not to be deterred and with his horniness growing by the second, Andrew reassessed the situation. He looked at his surroundings, underneath him were his brightly colored unicorn sheets sitting on his small bed. At its far end sat his pillow, Its cover was themed to match the the sheets, with pastel rainbows and a big happy unicorn prancing among them. As if his clitty was thinking for him, Andrew grabbed the pillow and slid it between his legs. He had never attempted anything like this before, but he had a strange feeling it could work.

He began to rock back and forth. His pullup rubbed against the pillow making a slight crinkling noise. Despite the source being through both his cage and diaper, Andrew instantly found it one hundred times more pleasurable than his hand. He gasped as he felt the pleasure hit him, this was the outlet his clitty had wanted for months, and desperately needed since the prior morning.

His pervy thoughts fully released themselves now, Andrew first thought of the kissing again but then imagined Lisa fondling him, and him fondling Lisa, their clitty, and the nipples on their tiny breasts. He imagined them in bed, Lisa's blonde hair draped haphazardly and their big smile as they entwined with each other. He even imagined them naked, clitties pressed together and humping just as he was now.

He humped slowly at first then began to move faster, the pullup clumped together and expanded over and over again. His hard penis clenched against its cage which held tight against the diaper, helplessly along for the ride and drenched in precum.

He moaned softly, then louder, and louder. To the point where he was surprised that it had not awoken any of the other sissies. Not that he would care if it did, the sensations he felt overcame all fear. The whole bed shaked and Andrew found himself glad that the springs didn't squeak. Within minutes, Andrew was climaxing over and over again, and he could feel the end was near. Could he really cum this way? Andrew thought between his moans and thrusts.

Then, one final imaginary scene came into Andrew's mind. With Lisa looking down at him and placing their dick in his mouth, then thrusting. At the thought of this, Andrew let out an effeminate gasp as he felt the overwhelming pleasure explosion.

His clitty finally let loose the floodgates and squirted its load into his pullup. More and more came out as he continued to hump, rubbing the fresh semen back up against his clitty, coating it.